Tert-Butyl nitrite → HCID 11951640, compound

HRID 1669056Notes

Reaction equation

N(OC(C)(C)C)=O.[N+:8]1([O-:22])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][C:12]=2[N:11]=[C:10](N)[N:9]=1)[CH2:18][CH2:17][CH2:16]3>CN(C=O)C>[N+:8]1([O-:22])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][C:12]=2[N:11]=[CH:10][N:9]=1)[CH2:18][CH2:17][CH2:16]3

Participants

Conditions

Temperature: 60 °C

Procedure

tert-Butyl nitrite (90%, 2 mL, 14.8 mmol) was added to a stirred solution of amine 19 (1.0 g, 4.95 mmol) in DMF (50 mL) at 60° C. and the solution stirred at 60° C. for 2 h. The solution was cooled to 20° C. and the solvent evaporated. The residue was partitioned between EtOAc (150 mL) and water (150 mL), the organic fraction was washed with water (2×50 mL), washed with brine (50 mL) and dried and the solvent evaporated. The residue was purified by chromatography, eluting with 10% EtOAc/DCM, to give 1-oxide 64 (401 mg, 43%) as a white solid: mp (EtOAc/pet. ether) 130-131° C.; 1H NMR δ 8.91 (s, 1H, H-3), 8.28 (s, 1H, H-9), 7.82 (s, 1H, H-5), 3.11-3.19 (m, 4H, H-6, H-8), 2.24 (p, J=7.5 Hz, 2H, H-7); 13C NMR δ 154.9, 153.0, 150.0, 147.3, 134.6, 123.2, 114.4, 33.2, 32.9, 25.7. Anal. calcd for C10H9N3O: C, 64.2; H, 4.9; N, 22.5. Found: C, 64.1; H, 4.9; N, 22.5%.

Workup

temperatureThe solution was cooled to 20° C.
customthe solvent evaporated
customThe residue was partitioned between EtOAc (150 mL) and water (150 mL)
washthe organic fraction was washed with water (2×50 mL)
washwashed with brine (50 mL)
customdried
customthe solvent evaporated
customThe residue was purified by chromatography
washeluting with 10% EtOAc/DCM

Sources & evidence

ORD record: ord-1bf6cda46d4f4269b9e43b61ea4dc89b
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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